Antibody Catalyzed Cationic Cyclization

• Published in: Science (American Association for the Advancement of Science) Vol. 264; no. 5163; pp. 1289 - 1293
• Main Authors: Li, Tingyu, Janda, Kim D., Ashley, Jon A., Lerner, Richard A.
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Society for the Advancement of Science 27.05.1994; Amer Assoc Advancement Science; American Association for the Advancement of Science; The American Association for the Advancement of Science
• Subjects: Alkenes; Animals; Antibodies; Antibodies, Catalytic - chemistry; Antibodies, Monoclonal - chemistry; Biological and medical sciences; Biotechnology; Catalysis; Catalysts; Cations - chemistry; Chromatography, Gas; Cyclization; Enzyme engineering; Esters; Fundamental and applied biological sciences. Psychology; Haptens; Kinetics; Logical Thinking; Methods. Procedures. Technologies; Mice; Miscellaneous; Multidisciplinary Sciences; Organic chemistry; Organosilicon Compounds - chemistry; Reaction mechanisms; Research Article; Science & Technology; Science & Technology - Other Topics; Silanes; Silicon; Sulfanilic Acids - chemistry; Sulfonates; CYCLASE; OXIDOSQUALENE; CANDIDA-ALBICANS; BAIT; STRATEGY; Abzyme; Cations; Catalysis; Enzymatic activity; Cyclization; Mechanism
• ISSN: 0036-8075; 1095-9203
• DOI: 10.1126/science.8191282

Two major goals for the design of new catalysts are the facilitation of chemical transformations and control of product outcome. An antibody has been induced that efficiently catalyzes a cationic cyclization in which an acyclic olefinic sulfonate ester substrate is converted almost exclusively (98 percent) to a cyclic alcohol. The key to the catalysis of the reaction and the restriction of the product complexity is the use of antibody binding energy to rigidly enforce a concerted mechanism in accord with the design of the hapten. Thus, the ability to direct binding energy allows the experimenter to dictate a reaction mechanism which is an otherwise difficult task in chemistry. New catalysts for cationic cyclization may be of general use in the formation of carbon-carbon and carbon-heteroatom bonds leading to multiring molecules including steroids and heterocyclic compounds.